Since the early 2000s, there has been increasing scholarly focus on the representations of masculinities in children’s literature. In part, this is due to the growing field of critical studies in men and masculinities coupled with wider public concern about boys’ development and education. This paper contributes to this work by analysing constructions of masculinity in four popular humorous series for children: Diary of a Wimpy Kid (2007–2022), The Treehouse books (2011–2023), The Bad Guys (2015–2023), and Planet Omar (2019–2023). Understanding genre as a reciprocal dynamic, the analysis demonstrates how these texts both intercede and shape the social and national milieu in which they are produced. As our understanding of acceptable masculine behaviours has adapted, so too has there been a shift in both the represented masculine dynamics and role of comedy in humorous junior fiction for boys. While some early series attempt to invert the hierarchical ordering of boys to validate alternative masculinities, the farcical genre conventions rest on limited models of masculinity, and frequently reaffirm the very tropes and behaviours that they seek to redress. In contrast, later series attempt to expand the repertoire of qualities that are acceptable for boys and men, challenging patterns of masculine hegemony, thereby revisioning what it means to be male. While humorous texts for young people may engage young male readers, the operation of humour and its relationship to masculinities is political, and can operate in either reductive or expansive ways.